US3156745A - Process for the manufacture of shaped structures of polyolefins having improved dyeing properties - Google Patents
Process for the manufacture of shaped structures of polyolefins having improved dyeing properties Download PDFInfo
- Publication number
- US3156745A US3156745A US73966A US7396660A US3156745A US 3156745 A US3156745 A US 3156745A US 73966 A US73966 A US 73966A US 7396660 A US7396660 A US 7396660A US 3156745 A US3156745 A US 3156745A
- Authority
- US
- United States
- Prior art keywords
- polyvinyl
- polyolefins
- vinyl
- filaments
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L31/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers
- C08L31/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C08L31/04—Homopolymers or copolymers of vinyl acetate
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
- D01F6/46—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polyolefins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/09—Polyolefin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/10—Polyvinyl halide esters or alcohol fiber modification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/21—Nylon
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/928—Polyolefin fiber
Definitions
- the object of the present invention is a process for preparing shaped structures, in particular filaments, that can readily be dyed.
- 0.1 to 30% by weight, preferably to 15% by weight, of a polyvinyl ester is admixed with the polyolefins to be shaped, the precentages being calculated on the quantity by weight of the polyolefins.
- the resulting mixtures can very well be worked up from a melt or solution into filaments or fibers.
- the admixture of polyvinyl esters having a low melting point does not impair the spinning properties of the polyolefins, as would have been expected.
- the spinning properties of the polyolefins are not even impaired if larger quantities of the polyvinyl esters of low melting point are added.
- the filaments that are obtained by the process according to the invention can be dyed, in particular with dispersion dyestuffs, and thereby be provided with depths of colour which it has hitherto not been possible to produce on polyolefin fibers.
- the physical properties of the filaments obtained in particular their tensile strength, are practically not impaired.
- Particularly good tinctorial effects are obtained by adding copolymers of vinyl esters with unsaturated carboxylic acids, in particular crotonic acid, to the polyolefin to be shaped.
- the mixture of the polyvinyl esters and/or copolymers thereof with unsaturated carboxylic acids with the polyolefins is advantageously carried out in the following way:
- the said esters and/ or copolymers which are in the dissolved state are sprayed on the polyolefin which is present in pulverulent or granular form, the polyvinyl esters are allowed to dry and the polymers are then thoroughly mixed.
- the polyvinyl esters and/ or copolymers may be admixed in a finely powdered form with the polyolefins.
- the filaments that were thus obtained had a tensile strength of 3.1 grams per denier and an elongation at break of 35%. They could well be dyed fast tints by means of dispersion dyestuffs, for example, a dyestuif of the following formula 3 NHz
- dispersion dyestuffs for example, a dyestuif of the following formula 3 NHz
- 100 parts of the granulate of linear polypropylene having a reduced specific viscosity of 1.9 were sprayed with a solution of 15 parts of polyvinyl acetate in parts of methyl acetate and the solvent was evaporated. The mass was then melted in an extruder, extruded and again worked up into a granulate which was transformed into filaments by the melt spinning process.
- the filaments that were thus obtained had a tensile strength of 3.8 grams per denier and an elongation at break of 25%. They could well be dyed by means of dispersion dyestuffs.
- Example 3 100 parts of pulverulent linear polypropylene having a reduced specific viscosity of 1.9 (measured in a solution of 0.1% strength in dekalin at 135 C.) were intimately mixed with 5 parts of finely powdered polyvinyl propionate. The mixture was then spun into filaments in the manner described in Example 2. The resulting filaments could be provided with great depths of colour by means of dispersion dyestuffs.
- Example 4 100 parts of pulverulent linear polypropylene having a reduced specific viscosity of 1.9 (determined in the way indicated in Example 2) were mixed with a solution of 5 parts of a copolymer of 95 parts of vinyl acetate and 5 parts of crotonic acid in 50 parts of acetone, the parts being calculated on the copolymer, and the solvent was evaporated. The mixture was spun from the melt into filaments which had an excellent capacity of being dyed by means of dispersion dyestuffs.
- an additive consisting essentially of a polyvinyl ester selected from the group consisting of polyvinyl acetate, polyvinyl propionate, polyvinyl butyrate, polyvinyl stearate and co-
- a composition of matter consisting essentially of a linear polyolefin selected from the group consisting of polyethylene and polypropylene having admixed therewith from 0.1 to 30% by weight of an additive consisting
Description
United States Patent vormals Meister Lucius & Briining, Frankfurt am Main,
Germany, a corporation of Germany No Drawing. Filed Dec. 6, 1960, Ser. No. 73,966 Claims priority, application Germany, Dec. 10, 1959,
6 Claims. 61. zen-s97 The present invention relates to a process for improving the properties of shaped structures of polyolefins, in particular the properties of filaments made of superpolymers of this kind. The invention also provides a process for the manufacture of filaments and fibers of polyolefins which can readily be dyed.
It is known to improve dyeability of polyolefins by admixing, for example, alkylene imines, polyamides, polyamino triazols, polyurethanes or polyureas, with the polyolefins, melting the resulting mixtures and working them up into filaments.
It has, however, become apparent that the filaments obtained by the aforesaid process can be dyed with colours of little depth only and that, moreover, the fastness properties of the dyeings are insufficient.
The object of the present invention is a process for preparing shaped structures, in particular filaments, that can readily be dyed. According to the invention, 0.1 to 30% by weight, preferably to 15% by weight, of a polyvinyl ester is admixed with the polyolefins to be shaped, the precentages being calculated on the quantity by weight of the polyolefins. The resulting mixtures can very well be worked up from a melt or solution into filaments or fibers. The admixture of polyvinyl esters having a low melting point does not impair the spinning properties of the polyolefins, as would have been expected. The spinning properties of the polyolefins are not even impaired if larger quantities of the polyvinyl esters of low melting point are added. The filaments that are obtained by the process according to the invention can be dyed, in particular with dispersion dyestuffs, and thereby be provided with depths of colour which it has hitherto not been possible to produce on polyolefin fibers. By the admixture of the polyvinyl esters the physical properties of the filaments obtained, in particular their tensile strength, are practically not impaired. Particularly good tinctorial effects are obtained by adding copolymers of vinyl esters with unsaturated carboxylic acids, in particular crotonic acid, to the polyolefin to be shaped. In some cases the additives according to the invention lead to the formation of products which, in addition to an improved dyeabil'ity, possess an increased thermostability. As polyvinyl ester polyvinyl acetate is preferably used. l olyvinyl esters of homologous carboxylic acids, for example, polyvinyl propionate, polyvinyl butyrate and polyvinyl stearate, and/ or copolymers of the aforesaid monomeric products with unsaturated carboxylic acids may also be used. The mixture of the polyvinyl esters and/or copolymers thereof with unsaturated carboxylic acids with the polyolefins is advantageously carried out in the following way: The said esters and/ or copolymers which are in the dissolved state are sprayed on the polyolefin which is present in pulverulent or granular form, the polyvinyl esters are allowed to dry and the polymers are then thoroughly mixed. Alternatively, the polyvinyl esters and/ or copolymers may be admixed in a finely powdered form with the polyolefins.
The following examples serve to illustrate the invenice tion but they are not intended to limit it thereto, the parts being by weight.
Example 1 parts of pulverulent lineaur polyethylnee having a reduced specific viscosity of 1.2 (determined in a solution of 0.1% strength in dekalin at C.) were sprayed, while stirring, with a solution of 5 parts of polyvinyl acetate (molecular weight about 200,000) in 50 parts of acetone. After evaporation of the solvent the mass was thoroughly mixed in a mixer for the purpose of homogenization. The mixture that had thus been pretreated was spun at 260 C. on a heated extruder which was provided with a nozzle, the resulting filaments were drawn oil? at a speed of 1000 meters per minute and subsequently stretched at 100 C. to four times their original length. The filaments that were thus obtained had a tensile strength of 3.1 grams per denier and an elongation at break of 35%. They could well be dyed fast tints by means of dispersion dyestuffs, for example, a dyestuif of the following formula 3 NHz Example 2 100 parts of the granulate of linear polypropylene having a reduced specific viscosity of 1.9 (measured in a solution of 0.1% strength in dekalin at 135 C.) were sprayed with a solution of 15 parts of polyvinyl acetate in parts of methyl acetate and the solvent was evaporated. The mass was then melted in an extruder, extruded and again worked up into a granulate which was transformed into filaments by the melt spinning process. The filaments that were thus obtained had a tensile strength of 3.8 grams per denier and an elongation at break of 25%. They could well be dyed by means of dispersion dyestuffs.
Example 3 100 parts of pulverulent linear polypropylene having a reduced specific viscosity of 1.9 (measured in a solution of 0.1% strength in dekalin at 135 C.) were intimately mixed with 5 parts of finely powdered polyvinyl propionate. The mixture was then spun into filaments in the manner described in Example 2. The resulting filaments could be provided with great depths of colour by means of dispersion dyestuffs.
Example 4 100 parts of pulverulent linear polypropylene having a reduced specific viscosity of 1.9 (determined in the way indicated in Example 2) were mixed with a solution of 5 parts of a copolymer of 95 parts of vinyl acetate and 5 parts of crotonic acid in 50 parts of acetone, the parts being calculated on the copolymer, and the solvent was evaporated. The mixture was spun from the melt into filaments which had an excellent capacity of being dyed by means of dispersion dyestuffs.
We claim:
1. A process for preparing readily dyeable filamentary structures of linear polyolefins selected from the group consisting of polyethylene and polypropylene, which consists essentially of admixing 0.1 to 30% by weight, calculated on the quantity by weight of polyolefins, of an additive consisting essentially of a polyvinyl ester selected from the group consisting of polyvinyl acetate, polyvinyl propionate, polyvinyl butyrate, polyvinyl stearate and co- 3 polymerso'f vinyl esters selected from the group consisting of vinyl acetate, vinyl propionate, vinyl butyrate and vinyl stearate with unsaturated carboxylic acids with the polyolefins to be shaped and working up the polymer mixture into shaped structures by the melt spinning process.
2. The process of claim 1 wherein 5 to 15% by weight of a polyvinyl ester is admixed with the polyolefins to be shaped.
3. The process of claim 1 wherein 5 to 15% by weight of a copolymer of vinyl acetate and crotonic acid is admixed with the polyolefins.
4. The process of claim 1 wherein the polyolefin is linear polyethylene.
5. The process of claim 1 wherein the polyolefin is linear polypropylene.
6. A composition of matter consisting essentially of a linear polyolefin selected from the group consisting of polyethylene and polypropylene having admixed therewith from 0.1 to 30% by weight of an additive consisting References Cited in the file of this patent UNITED STATES PATENTS 2,448,666 Fletcher et a1 Sept. 7, 1948 2,569,470 Hagerneyer et a1. Oct. 2, 1951 2,772,247 Schroeder Nov. 27, 1956 2,944,040 Pollock et al July 5, 1960 2,975,150 Johnson et al Mar. 14, 1961 FOREIGN PATENTS 1,050,002 Germany Feb. 5, 1959
Claims (1)
- 6. A COMPOSITION OF MATTER CONSISTING ESSENTIALLY OF A LINEAR POLYOLEFIN SELECTED FROM THE GROUP CONSISTING OF POLYETHYLENE AND POLYPROPYLENE HAVING ADMIXED THEREWITH FROM 0.1 AND 30% BY WEIGHT OF AN ADDITIVE CONSISTING ESSENTIALLY OF A POLYVINYL ESTER SELECTED FROM THE GROUP CONSISTING OF POLYVINYL ACETAE,POLYVINYL PROPIONATE, POLYVINYL BUTYRATE, POLYVINYL STEARATE, AND COPOLYMERS OF VINYL ESTERS SELECTED FROM THE GROUP CONSISTING OF VINYL ACETATE, VINYL PROPIONATE, VINYL BUTYRATE AND VINYL STEARATE WITH UNSATURATED CARBOXYLIC ACIDS TO IMPROVE THE DYEABILITY OF THE POLYOLEFIN.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF30048A DE1106450B (en) | 1959-12-10 | 1959-12-10 | Process for the production of structures made of polyolefins that are easy to dye |
Publications (1)
Publication Number | Publication Date |
---|---|
US3156745A true US3156745A (en) | 1964-11-10 |
Family
ID=7093580
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US73966A Expired - Lifetime US3156745A (en) | 1959-12-10 | 1960-12-06 | Process for the manufacture of shaped structures of polyolefins having improved dyeing properties |
Country Status (4)
Country | Link |
---|---|
US (1) | US3156745A (en) |
BE (1) | BE598061A (en) |
DE (1) | DE1106450B (en) |
GB (1) | GB968387A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3382298A (en) * | 1964-12-17 | 1968-05-07 | Union Carbide Canada Ltd | Stress-crack resistant polyethylene containing a polyvinyl acetal |
US3765829A (en) * | 1969-12-09 | 1973-10-16 | Ethylene Plastique Sa | Colourable polyolefin compositions |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB980971A (en) * | 1961-02-13 | 1965-01-20 | Kurashiki Rayon Kk | Method of manufacturing synthetic fibres and shaped articles of polyolefin having improved dyeability |
DE1223102B (en) * | 1963-05-11 | 1966-08-18 | Bayer Ag | Manufacture of threads or fibers by melt spinning polypropylene and an additive |
DE1223491B (en) * | 1963-05-11 | 1966-08-25 | Bayer Ag | Manufacture of threads or fibers by melt spinning polypropylene |
NL6414527A (en) * | 1963-12-31 | 1965-07-02 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2448666A (en) * | 1944-06-14 | 1948-09-07 | Du Pont | Polyethylene-polyvinyl acetal composition |
US2569470A (en) * | 1950-06-07 | 1951-10-02 | Eastman Kodak Co | Compositions comprising acrylonitrile and hydrolyzed polyvinyl acetate |
US2772247A (en) * | 1951-11-20 | 1956-11-27 | American Can Co | Anti-blocking adhesive composition containing polyethylene, tackifying resin, and a polyvinyl ester |
DE1050002B (en) * | 1959-02-05 | |||
US2944040A (en) * | 1956-09-17 | 1960-07-05 | Phillips Petroleum Co | Method of preparing high solids latices of film-forming polymers and high density ethylene polymers |
US2975150A (en) * | 1956-06-11 | 1961-03-14 | B B Chem Co | Thermoplastic adhesive compositions and supply articles |
-
0
- BE BE598061D patent/BE598061A/xx unknown
-
1959
- 1959-12-10 DE DEF30048A patent/DE1106450B/en active Pending
-
1960
- 1960-12-06 US US73966A patent/US3156745A/en not_active Expired - Lifetime
- 1960-12-09 GB GB42555/60A patent/GB968387A/en not_active Expired
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1050002B (en) * | 1959-02-05 | |||
US2448666A (en) * | 1944-06-14 | 1948-09-07 | Du Pont | Polyethylene-polyvinyl acetal composition |
US2569470A (en) * | 1950-06-07 | 1951-10-02 | Eastman Kodak Co | Compositions comprising acrylonitrile and hydrolyzed polyvinyl acetate |
US2772247A (en) * | 1951-11-20 | 1956-11-27 | American Can Co | Anti-blocking adhesive composition containing polyethylene, tackifying resin, and a polyvinyl ester |
US2975150A (en) * | 1956-06-11 | 1961-03-14 | B B Chem Co | Thermoplastic adhesive compositions and supply articles |
US2944040A (en) * | 1956-09-17 | 1960-07-05 | Phillips Petroleum Co | Method of preparing high solids latices of film-forming polymers and high density ethylene polymers |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3382298A (en) * | 1964-12-17 | 1968-05-07 | Union Carbide Canada Ltd | Stress-crack resistant polyethylene containing a polyvinyl acetal |
US3765829A (en) * | 1969-12-09 | 1973-10-16 | Ethylene Plastique Sa | Colourable polyolefin compositions |
Also Published As
Publication number | Publication date |
---|---|
DE1106450B (en) | 1961-05-10 |
BE598061A (en) | 1900-01-01 |
GB968387A (en) | 1964-09-02 |
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